


Helping out a Friend

by limsteven73



Category: Original Work
Genre: Anal Fingering, Anal Sex, Anal creampie, Bisexual Male Character, Childhood Friends, F/M, Gay Male Character, Gay Sex, Long, M/M, Other, Shemale, Shemale on Male, Trans Character, Trans Female Character, Transgender, blowjob
Language: English
Status: Completed
Published: 2017-12-28
Updated: 2017-12-28
Packaged: 2019-02-22 22:52:14
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 10,928
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13176885
Author URL: https://archiveofourown.org/users/limsteven73/pseuds/limsteven73
Summary: Her name was Samantha Bolton, my childhood friend and neighbour since the day we were born. With birthdays only a week apart, you could say that the two of us were the definition of childhood friends, our earliest memories involving each other. I still remember the days when we were still children, the times when we would dash around the fields and jump into rivers, the looks of despair and concern on our mothers’ faces when we returned home soaked and covered in mud, the beatings we would get just opposite from each other and the smiles we gave each other after it was all over, the memories of childhood still fresh in my mind.The only difference was that there was not a young girl in my memories…But a young boy…After a coming out, a confession and a large fight, I found myself alone. Desperate to find him and apologize, i found myself missing that young boy in my memories... this wasn't love... or at least that's what I keep telling myself...





	Helping out a Friend

“Ahh~ Right there… I can’t… Your mouth… Your mouth feels so… so good~” My childhood friend and neighbour of more than eighteen years moans as she grabs the back of my head tightly, tufts of my hair stuck between her fingertips. I groaned in discomfort as the constant flow of pleasure, created by my tongue playing with her sensitive pleasure bits, causes her to pull on my hair, the pain from my scalp coaxing out a groan from my lips, which in turn gives her more pleasure and repeats the cycle. “Lick me more~”

“Mmm…” I comply as I voice my response into her body, the vibrations caused by my muffled words making the young woman twitch and jerk in pleasure, drool leaking from the corners of her mouth as she begins to lose control of her body. With an occasional clamp on my skull and a decent massage caused by her constantly shifting legs, I continue to provide my childhood friend with the pleasure she desired, the pleasure her body craved. It was only until I felt her thighs squish my head with its powerful hold, and the sudden increase in both pitch and frequency of her moans, did I pull away from the young woman, a sadistic side of me loving to tease and deny her of her much needed release. 

“WHY’D YOU STOP?!” My childhood friend screams in frustration as she tries to grab hold of my head with her hands, but I had already since escaped her grappling range. I smirked at the young woman as she glares at me, frustrated that I had left her hanging. In an attempt to capture me and force me down, the young woman leaps from the bed she was sitting on, her eyes that of a hungry predator targeting its escaping prey. However, because I was just pleasuring her for the past few minutes, her legs were not as stable as they normally were, thus the young woman falls face first towards the ground. “Owowow… Help me…” The young woman requests as she supports herself on her hands and knees, helpless and aroused. 

“Help you with what?” I tease even further in response as I place my fingers against her crotch, my fingertips only barely grazing at her sensitive flesh as I avoid giving my childhood friend any more than a teasing amount of pleasure. “I won’t understand unless you tell me…” 

“Can you… Pleasure me…” My childhood friend begs as she stares at me, a sinister thought sprouting into my mind. Without saying anything, I quickly flip the young woman over such that she was laying on her back, before proceeding to lean over her, my face directly above hers. With a flushed face and the sound of her heart beating rapidly in her chest, the young woman gently shuts her eyes as she puckers her lips, inviting me for a kiss she expected me to give. Leaning in, however, I lower my face until my eyes were in line with her perky breasts, her AA-cup boobs small and almost unnoticeable. “Why are you going for those miserable nubs… you know I don’t feel much from them…” My childhood friend asks, slightly disappointed that I wasn’t going for a kiss judging by her sad expression, her nipples barely even hard even though she was plenty aroused. 

“Well… I just want to…” I teasingly smile at the young woman as I wrap my lips around her small nipple, the tiny nub barely even able to reach past my teeth. Suckling and nibbling, I coat the young woman’s tiny mound with my saliva, soft moans and groans escaping the young woman’s lips even though she was barely feeling anything. 

“Can you… Suck my…” The young woman meekly asks with a voice barely above that of a whisper, her eyes glancing towards me before turning away, almost as if she was asking for something more embarrassing than the sex we were currently enjoying. I could feel my own member stiffen once I had witnessed the young woman’s adorable expression, her embarrassed face one of her cutest, the desire to tease her even more sprouting from the tiny seed in my lusty heart.

“What is it that you want me to suck?” I tease as I lick at her nipples, before trailing my tongue up and down her body, teasing each and every body part I could find. “Here?” I ask as I gently lick her waistline. “Or here?” I giggle as I nibble at her inner thigh, a short and silent squeal escaping the young woman’s lips. I giggle as I continue to tease the young woman, her blush deepening as I caress and suckle all the nooks and crannies her body had to offer. “Or maybe…” However, after a brief moment of fun, I focus my tongue onto her favourite body part, my lips gently kissing at the enlarged and dark red tip. “Here…?”

“YES! SUCK MY COCK! WRAP YOUR LIPS AROUND MY DICK AND LET ME FUCK YOUR MOUTH!” My childhood friend screams dirty words unfitting of a young woman as she voices out her needs, her voice so loud, I was afraid the neighbours would hear. I laugh loudly as I watch my childhood friend’s face turn a deep shade of intense crimson red, the blood rushing to her already flushed face as embarrassment completely washes over her.

“How subtle…” I half-smirk at the young woman as I wrap my fingers around an unexpected appendage attached to her crotch, my grip squeezing her throbbing hot rod of flesh with almost all of my strength, the pain, or maybe it was the intense pleasure, rushing through her body in an instant as her slim body jerks around violently, a fountain of white cream eagerly attempting to pour out of her body, only to be stopped by my death grip right around the middle of her shaft. 

“LET ME CUM! IT HURTS! LET ME CUM!” My childhood friend begs as I oblige her request, however, not before aiming her own cock towards her face and forcing the young woman to give herself a facial. “AAHHHH!” The young woman screams as her sperm explodes out of her shaft, the thick white cream firing directly into her mouth and over her face, her pale white skin now even whiter. 

……

Her name was Samantha Bolton, my childhood friend and neighbour since the day we were born. With birthdays only a week apart, you could say that the two of us were the definition of childhood friends, our earliest memories involving each other. I still remember the days when we were still children, the times when we would dash around the fields and jump into rivers, the looks of despair and concern on our mothers’ faces when we returned home soaked and covered in mud, the beatings we would get just opposite from each other and the smiles we gave each other after it was all over, the memories of childhood still fresh in my mind.

The only difference was that there was not a young girl in my memories…

But a young boy…

Born into the world as a young man, with the birth name of Samuel Bolton, my childhood friend of eighteen years was indeed male… at least until his nineteenth birthday. Neither myself nor his family had ever even considered that he was harbouring such a secret, but after he came out, it all made sense. His coming out of the closet story was classic but still shocking nonetheless, suddenly gathering his parents, my parents and I into the living space of his home, Samuel sat in silence as he fumbled with his words. With cold sweat dripping from his body as he nervously tries to find the words to say, his body fidgeting awkwardly as he avoids the concerned and suspicious gazes from the people around him, all classic signs of someone confessing a deeply held secret.

“Mom, Dad… I’m gay…” He said, his voice almost cracking as he nearly broke down from all the stress he was feeling. It was almost like the time we had taken a rather difficult examination paper, the panic in Samuel’s eyes almost exactly the same as it was at that time. Before his parents had even responded, and before he lost his momentum, Samuel quickly turns to face me and my parents, yet another shocking confession slowly rising up his throat. “And I’m in love with my childhood friend, Steven.” 

An awkward silence took over the tense atmosphere, none of us knowing how to react to what the young man had just said. I stared at my childhood friend in surprise, not a single fibre in my body even realising that not only was he attracted to members of the same sex, but also attracted to me in particular. I gave my parents confused looks, the two of them returning it to me with expressions even more confused that I was. His mother and father were speechless, the latter of which was already beginning to grow red in anger and embarrassment. 

“WHAT IS WRONG WITH YOU?!” Samuel’s dad suddenly bursts out screaming as he angrily slams his newspaper into the ground, his face bright red with anger as small veins pop out from the side of his head. His mother quickly jumps up to stop his father’s raised hand, although she was feeling as shocked as the rest of us were. “I DID NOT RAISE MY SON TO BE LIKE THIS!” 

“DEAR! CALM DOWN!” Samuel’s mother screams in response to her husband’s outburst as she tries to hold him back, although her hateful glare was all that we needed to know that she had the same opinion as the enraged man, her eyes telling us to take her useless son away. My parents were visibly shocked, not only were they frightened by their close friend’s sudden eruption, they were appalled at how cruel Samuel’s parents were being to him. 

“Come…” My mother quickly shielded Samuel’s eyes from the utter chaos that was currently unfolding before him, protecting him from the violent emotional assault his parents were unintentionally giving, as she ushered us away, leaving the storm of a household to calm down on its own. “We’ll take care of you… until all the bad things go away…”

……………

For the next few days, Samuel sought refuge in the comforts of my home, of course in a separate room due to my parents’ fear of a sudden sexual assault, his family currently in a disastrous state. His father was furious at his son’s sudden confession, his rage lasting for almost a week, while his mother could only cry at the reality. The two of them would argue on end, neither of them willing to accept the blame for turning their son gay. The police were often called in and my parents quickly turned their backs to the couple that were once their closest friends, neither of them willing to get involved in such a fragile and tense situation. 

Samuel, on the other hand, was taking the situation rather well, his smile never leaving his face even though he was now basically running away from home, his parents abandoning him. The two of us would attend classes like normal, eat meals together like normal, play games together like normal and even talk about girls together like normal, almost as if the whole coming out of the closet and confession event never even happened. 

At least, that’s what it appeared like from the outside.

In reality, the two of us could have never been more awkward. Our eyes would no longer meet even when passing each other at home, our travel to school would be silent and awkward, our meals and games would have an awkward atmosphere around it and our regular guys talk would only create an odd tension in the air, a rather sexual one as Samuel’s eyes constantly darted over my body. 

“I can’t take this anymore…” Samuel, out of the blue, remarks whilst we were in the middle of a conversation about breasts and butts, a conversation we would have once enjoyed laughing and teasing each other about. “It’s been two months since I confessed to you… Can I at least get a rejection? At least that will make my heart stop wavering and quivering whenever I’m with you…” Samuel asks as he stares me in the eye, before lowering his gaze to the floor. I gulped as I face the moment I had been anticipating for, the awkward tension in the air for the past few weeks preparing me for this moment. 

“Samuel… I…” I began, before chocking on my own words. All the plans and situations I had imagined and prepared myself for, all the sleepless nights I spent thinking about a way to reject my best friend in the kindest and least hurtful way possible, all the time I had spent thinking about him and his confession… all of it came to naught when it all came down to the wire. I couldn’t say I was rejecting him, his tear-stricken and depressed expression flooding my mind as I imagine a life where we were no longer friends. No… I can’t imagine a life where we weren’t friends… If that’s how this will all end…

“I accept your confession…”

……

The two of us then began to date in secret, though I still couldn’t get over the fact that my best friend was now my partner… and that he was a guy. Although I tried my hardest to ignore the fact that I was currently attached to another man, there was no possible way my mostly straight mind would let me feel any bit aroused or excited whenever the air became sexual, my lips and his never even connecting merely because the act of kissing another guy completely grossed me out. Samuel probably realised I was feeling that way, judging by his lack of enthusiasm when we went on dates and his passive approaches to try and appeal to me. However, I still wasn’t able to really fall in love with him, the young man reminding me too much of our carefree childhood days and times when it wasn’t as tense between us. 

“Sorry… This isn’t working out like how I imagined it to be…” Samuel suddenly admits after one of our dates, his eyes already beginning to tear up as he initiates the break up. We then spent about the next two hours talking, the two of us pouring our hearts and innermost feelings to each other without holding back. He talked about how he wanted to kiss me, hug me, embrace me, cuddle with me and, ultimately, make love to me, while I, on the other hand, was feeling the complete opposite. 

In the end, I didn’t manage to break past the barrier known as gender, my love for the young man almost non-existent simply because I couldn’t imagine myself with another man. I told Samuel about how I simply couldn’t imagine kissing and embracing another guy without feeling some form of, no matter how little, disgust, my mind simply wired to feel that way. 

“I understand…” Samuel answers my confession with a fog in his throat, tears already streaming down his cheeks as he cried his eyes out. I, not knowing how to respond, could only sit there, I could only watch as my friend bawls his eyes out and suffer in silence. “I’ll get out of your way now…” Samuel screams as he dashes out of my room, the young man not even bothering to wear a pair of shoes as he runs away from the home that he built too many memories in, the pain too much for him to handle. 

“WAIT!” I screamed after him as I chased after my best friend, my feet almost slipping as I desperately run after the fleeting back of one of my most precious person, but his legs were much stronger and faster than mine, his large back quickly disappearing into the horizon as I could only watch him leave my side, an empty, cold seat now next to me.

…….

A couple years had passed without a word from the young man, my life moving on as I found my way in and out of college. I found a goal after that day, the conversation I had with my best friend that ruined our relationship causing me to find something I wanted to do with my life from then on out. Spending the remainder of my high school life absorbed into my studies, I quickly destroy the former procrastinator I once was and hit the books with vigour, my goal being the top college in my region. 

Never finding a girlfriend, never really searching for love, I then lived on with the label of ‘nerd’ plastered all over my body, my former friends and classmates quickly abandoning me and continuing on with their own youth. I didn’t care though, it didn’t matter to me how others thought of my new change, all that mattered was that I achieved my goal. However, the route to success and achievement was hard, some long nights leaving me screaming and suffering in intense anxiety pains, my brain completely numb and long burned out. 

“SAMUEL!” I would scream with all my remaining strength, my best friend’s name and the image of his fleeting back the only thing that would keep me going through the pain and loneliness. That one word, that one name, was all it took to calm my raging heart and mind, the reason for all my suffering belonging to that one man. Although some would feel intense hatred and biased anger, calling out the reason for my suffering only gave me the energy to push on, that painful image of my best friend leaving me as he ran off crying hurting much more than this temporary suffering. “I must go on… I must…” I repeated as I weakly continued my intense studies, the results of my efforts showing themselves with my acceptance into my first-choice college.

My years in college were no different from that in high school, my goal and drive unwavering as I ignored invites to clubs, parties, circles, orgies and even nerd night with the members of my dorm, my hands never letting go of a pen and my body never leaving the seat at my desk. 

“Why are you even studying so hard?” My roommate at the time would ask over and over again as he messed around with the women in his club, sometimes even having intense and wild sex behind my back as I attempted to focus my entire soul into my textbooks and lecture notes. “Is it for a girl?”

“I guess you could say that…” I coldly reply as I continued to write intricate notes onto my notebook, a small tear already forming at the corner of my eye as I recall my past. “All of this is so I can get back with my childhood friend… to make him happy…”

“Him?” My roommate questioned as he slowly began to avoid being near me, the most probable reason being a suspicion of my sexual preferences. I was grateful, however, when I was soon left alone to my own devices, my roommate never returning back to the bunk we shared and eventually leaving completely. I didn’t care though; I didn’t need his presence to achieve my goals…

……..

Studying, studying and studying late into the night, I made sure that I crammed every single last detail of my notes into my head, the final exam and one of the largest obstacles to achieving my goal now not too far away. I knew I could do it… I did not spend the last few years absorbed into my studies for nothing…

However, fate had a way to twist things around for its own sick entertainment…

“No way…” I could only mutter those two words in utter shock as the results of all of my effort shook me to the core. Taped to the large noticeboard was the results of the latest preliminary examination, a sort of mock test that my college gave to give the students a chance to see how they were currently faring before the big final exam a mere five months away, and on it… my name was in the bottom half. 

With grades far lower than I had expected and scores that could mean my expulsion, I was marked as a worthless waste of time by the lecturers and examiners of my school, my chance at obtaining even a slimmer of my goal quickly going up in smoke. 

For days after that, I could only wrap myself up in my blankets and rot in my bed, my energy all spent and my willpower all but eaten away by my own depression. I would skip meals and avoid calls from my course mates, although not a single one of them visited my room. My roommate stopped by once during my depression, although he only scoffed at me and packed up his things. 

“Serves you right…” He said to my bawling face as he left me in the cold and lonely darkness of my own sadness, not an ounce of sympathy in his voice. This was it; this was the end of everything that I had lived for. I worked so hard, abandoning all of my chances at a normal youth, a normal relationship, a normal life, I had worked so hard… but my efforts were all in vain…

“Samuel… I’m sorry…” I apologised as I cried myself to sleep, the image that I had been building inside my head for the past few years, the vision of my future that I had created, disappearing into the horizon like the back of my childhood friend.

………

“You tried to do what for me?” Samuel laughs at my face as he presses his foot against my face, the dirt on the sole of his shoe barely even affecting the grime that had been built on my body. It has been about ten years since I flunked out of college, my lack of adequate academic qualifications causing me to fail at all of the many job interviews I had went for. To make things worse, because of my stress, I had quickly picked up an addiction to gambling and drinking, my parents soon later disowning me and leaving me homeless on the streets. It was around that time I bumped into a familiar face, a more mature and grown-up version of Samuel appearing before me. “Someone useless like you trying to help me? That’s hilarious!

“But… but I tried to study… I wanted a future where I could help you… so we could be together again…” I confess my intentions to the man that I had worked my youth away for, the man that I spent years trying to find and get back to my side, but all he did was scoff and spit in my face. 

“Why? You never loved me, you never cared for me, you never bothered to understand me…” Samuel exposes his heart as he screamed his emotions at me, the pain he must have felt that day when we broke clearly hurting him deeply. “Forget it… it’s a thing of the past now… I found someone else that makes me much happier than you could ever even dream of doing.” 

“What? But… but I thought you loved me…” I desperately grab at Samuel’s legs as if I was trying to prevent my childhood and best friend from leaving my side once more, desperation in my heart sprouting from pure loneliness. 

“That was in the past… I don’t care about you anymore…” Samuel quickly turned away from my pitiful self, probably because he could no longer stomach seeing his first love in such a disastrous state for any longer. “Good luck, Steven…”

“SAMUEL!”

……..

“SAMUEL!” I screamed as I flew out from under my covers in tears, my heart beating rapidly in fear as the nightmare completely wrecks my mind from within. I hyperventilate as the pain from such a horrendous sight causes my body to go into a panic, the mere recollection of my dream striking fear into my blood. 

“Are you okay?” The voice of a young woman sends me flying towards the wall, my head slamming against the hard bricks with a loud noise. “ARE YOU OKAY?!” The young woman screamed as she hesitated to offer a hand to me, the shock from my reaction to only her voice causing her to subconsciously avoid further approach me. 

“WHO THE FUCK ARE YOU?!” I screamed as I examined the unfamiliar young woman from head to toe, not a single part of her ringing a bell in my head. With long black hair that cascaded past her modest small B-cup breasts, a tanned complexion paired with rather small facial features and Asian eyes, thick rimmed glasses and a slightly chubby figure, the young woman before me gave off a very cliché nerdy Asian girl image. 

“My name is Amelia Lee, your course mate… It kinda hurts when your own course mate doesn’t even recognise you… hahaha…” The young woman, who calls herself Amelia, gives a forced and awkward laugh as she clears her throat, her stare returning to meet my own as she looks at me with a serious expression. “I came here today to bring you back to class… finals are barely even three months away and I have yet to see you in lectures.”

“I’m not going back…” I reply coldly as I hide my eyes from her painful stare, the determination and confidence in her eyes hurting the now depressed and sad me. “Someone who looks smart like you probably wouldn’t understand, but studying with all my heart, all my soul, and having it return with no results is much more painful than you might imagine.”

“Who are you calling smart.” Amelia angrily questions as she grabs my collar, before pulling me towards her with strength one wouldn’t expect from a girl like her. “I don’t know if you’re mocking me or if you’re just clueless…” Amelia angrily screams into my ear as she forces my head to face her, her eyes filled with a new emotion of pain. ”Just like you, I did horribly for my prelims… My score was even lower than yours…” 

“No way…” I replied in utter disbelief, the confident and determined woman that entered my room did not seem like someone that scored badly, much less in the bottom percentage. 

“Yes way… But unlike you, I continued to study hard.” Amelia lectures as she pulls me out of bed, before dragging me towards my desk and throwing me onto my chair. “And now I’m at the top of the class.”

“NO WAY!” I scream in utter disbelief, thinking that this young woman was clearly lying through her teeth. Almost as if she was reading my thoughts, Amelia cracks a sly grin as she pulls out her smartphone, an image of the latest mock exam results placed next to the ones from the preliminary examinations, Amelia’s position rising from the bottom 100 to the top 50. “NO WAY!” 

“Hm.” Amelia smiles as she puts away her phone, before pressing her face closer to mine. “Now… I need you to score just like what I had managed to do.” Amelia forces a request upon me before pulling away from me, confusion plastered all over my face. 

“Huh?” I could only let out a small sound to voice out my confusion, but it seemed that Amelia would not take no for an answer, the young woman quickly pulling me out into the hallway and towards the school building, my clothes still dirty and my body in a mess. 

…..

With only a couple months left before the final exams, Amelia began coaching me like an academic drill sergeant, her Spartan ways of teaching leaving me exhausted by the end of the day and sore the next morning. With her help, I manage to integrate back into college life, my brain easily bouncing back as it quickly remembers old subjects I had learned whilst easily absorbing new information. 

My social life had also improved, Amelia’s assistance with my studies and our warm public interactions changing how the other students of my college began to see me. No longer was I the cold nerd that hated human interaction, a new me was yet again born. 

“Why are you helping me out like this anyway…?” I asked Amelia one day whilst the two of us were studying alone in the school’s library, all of my friends already leaving and home and leaving the two of us behind. “I don’t see why you would have ever involved yourself with someone like me…”

“Well… Uhh…” Amelia panics as I turn to face her, her face flushed and bright red in embarrassment. I cocked my head as I wondered why she was acting so panicky, I didn’t ask her for her first love or anything, all I asked for was why she was bothering to help someone as useless like me. 

“What’s wrong?” I follow up my question with another, this time intending to question her about her weird behaviour. “It’s not like you did it for a lame reason like wanting a rival or something right?” I joke, but this only made Amelia more nervous and hushed up. 

“I did it…” Amelia finally speaks up as she looks at me with determination in her eyes, an intense stare into my soul. “I did it because I thought you were cool when you were studying so desperately for what you wanted… I thought you were cool…” 

“Really? But I don’t think I can get what I want anymore… not with these grades…” I reply with what was intended to be a light-hearted joke, however my own remark quickly causes me to fall back into the pit of depression I was once hollowed inside. 

“That’s not true! You can get it! I can help you get it!” Amelia screams out her conviction as she grabs my hands with her own, her sudden scream causing me to turn and face her, my eyes now locking with hers as we stare into each other’s souls. “And when you get it… Can you go out with me…” Amelia’s conviction trails off as she stares at the ground in embarrassment. I didn’t expect a confession from her, not one bit, but yet it made me slightly happy. This was the first time a girl had confessed to me, and a rather cute one at that, my youth completely devoid of love…

Maybe this was the Gods telling me that I needed to move on, that someone else was better at filling the hole in my heart. With anxiety, depression, sadness and fear in my heart, I turn to face the young woman, her blushing face catching me off guard as my own heart began beating rapidly, a feeling I had never felt before easily overpowering all of the doubts of my own feelings, a sudden but intense desire to stand next to the person in front of me deciding my next choice. 

“I’ll be glad to.”

…….

The next month was hectic, the need to study and the desire to be together both mixing and clashing together at the same time. Whilst the two of us did meet up on more than one occasion, sometimes more than once a day, half of our time together was wasted with unproductive acts like flirting and kissing, Amelia more of a carnivore than I had imagined. 

Maybe it was because she had been pent-up after studying for so long, the young woman actually a closet pervert, her high sexual libido revealing itself to me when I had walked in on her masturbating to my underwear mere days after we had gotten together. It was not much of a shock to me, in fact I had found myself rather aroused by it, but it did change the way I had viewed the young woman. Kissing and making out became more frequent as we both began to let loose, our inhibitions completely tearing themselves apart as we discovered the joys of another person’s embrace. 

There were times when we would meet up with the intent to study, only to find ourselves wrapped in each other’s arms with a hand on the other’s various erogenous zones, one thing quickly leading to another as the days went by. It may have been one of the fastest developments in a normal relationship, the two of us ready to cross the line a mere week after getting together. 

Maybe it was the lust in our teenage bodies winning, but, before we had known it, the two of us found ourselves waltzing nervously into a small hotel, both of our dorm rooms unable to accommodate what we were about to do. 

“I’LL JUST TAKE A SHOWER!” Amelia screamed nervously as she awkwardly walked over to the attached bathroom, the sound of my rapidly beating heart drowning out the faint pitter-patter of the shower water as it trickled off Amelia’s body and onto the bathroom floor. I could feel my palms sweating as I began rubbing them on my clothes, before realising that I should prepare myself before Amelia returned. 

“Should I take these off…? Or does she take it off…” I rack my brain as I try to figure out the solution to a common problem encountered by many virgins that watch too much porn, the issue of who removes who’s underwear very prominent in modern times. I had seen many porn films where the woman would remove the guy’s underwear before giving him a blowjob… but does that apply here?

“KYAAA! WHAT ARE YOU DOING!” Amelia screams as she covers her eyes with her hands, my own body quickly moving to cover my groin on reflex. I turn to face Amelia, my own face blushed a deep red, as the sight of fully naked young woman burns itself into my memory. Her body wasn’t completely free of fat like a model’s, but she was rather slim. It seemed that her tanned skin was not limited to her normally exposed areas either, her entire body covered in a nice light brown. My eyes quickly jump from the three landmarks on the young woman, her two nipples, her neatly trimmed pussy and her nice round yet perky butt. “WHAT ARE YOU STARING AT?!”

“I’M SORRY!” I reply, embarrassed that I had become so mesmerized by her body that I found myself staring at her the whole time, my gaze probably perverted and my hard erection not backing me up at all. “It’s just that your body was so arousing and sexy and-“

“DON’T SAY THAT!” Amelia cuts me off with another of her loud screams, the air between us suddenly becoming more awkward. After about two minutes of deafening silence, Amelia was the first to giggle. “What are we doing…”

“Trust me, I don’t even know…” I reply back as we erupt into a roaring laughter, the awkward tension dissipating quickly. “Should I…?”

“No… Let me…” Amelia replies, her shaking hands telling me she was still slightly nervous about the whole ordeal. I couldn’t blame her though; even I could feel my legs quiver the closer she approaches. “I’m taking these off now…” Amelia informs as she slowly pulls my boxers off, my member flopping out of its prison and smacking the poor girl across her face. “Looks like someone is a little excited…” Amelia teases as she wraps her slender fingers around my shaft, the cold from her fingertips sending a chill down my spine. “Is this good?”

“Yeah…” I let out a soft groan as the sensation from having someone else touch my member brings forth a whole new realm of pleasure, the ticklish feeling of being unable to expect what was going to be done slightly arousing. “Can you… go a little harder…” 

“Like this?” Amelia asks for my approval as she slightly tightens her grip, although it wasn’t nearly enough. I try to gain as much stimulation from her touch as possible, a part of me wanting to prolong this blissful experience by weakening the stimulation done to my body. However, for some odd reason, there was a part of me that felt oddly disgusted by having my member stroked by Amelia, a still image of my childhood friend’s face flashing through my mind. “What happened?” Amelia asks as she looks up at me, a flaccid piece of man-meat in her hand. 

“Oh… I don’t know…” I avoid the question as I look away from the young woman, the guilt from imagining another person, a man no less, preventing me from telling her the truth. I hated to admit it, but I still couldn’t get him out of my mind, my childhood friend’s fleeting back from that day still haunting me. I knew that I had only latched onto this innocent young woman to try and escape from my emotions, but I guess it had finally caught up to me.

“I know you’re hiding something…” Amelia looks straight through me as if I was a piece of glass with skin attached to it, the guilt from earlier now completely filling my body. I glance over to my girlfriend, her expression a mixture of sadness and anger. I hold back my urge to cry, there was no way I could continue doing this to her… not with these mixed feelings in my heart.

“I’m sorry Amelia… We need to talk…”

……..

A month after that, with the help of my new friends and the pain from breaking Amelia’s heart now a part of the force pushing me forward, I graduated college with grades the top of my class. Amelia accepted my rejection without much of a fight or a crying fit, her tears forming quickly but she still managed to give me her trademark warm smile. The two of us continued to study together, and by the end of our study sessions, I could tell I had improved from my failure at the preliminary exams. With my life’s goal already right in front of me, my happiness ready to be shared with my family. I invited my family and Samuel’s family to my graduation ceremony, hoping that I could show them how my life has changed since that fateful day, and what I was planning to do from then on out. 

It was there where I met her…

Standing beside Samuel’s parents was a stunning beauty, a young woman with dirty blonde hair that grew past her waist and eyes that reflected confidence and hope. Although her shoulders were rather broad for a young woman and her chest small, the young woman’s tanned and toned body gave off a rather attractive aura. Her hips were almost boyish but still had some volume to it while her legs were long and shaved, her figure resembling that of a young woman who had just hit puberty. I glanced over the young woman’s body quickly, hoping to get a better look at her figure, only to realise she looked rather familiar…

“Ah! Steven!” The young woman cheerfully calls my name as she waves to me, I awkwardly wave back as I wonder where in the world I knew this woman from. “It’s so glad to see you again… it’s been like what? 4 years?” The young woman easily strikes up a conversation as if we had known each other for our whole lives, her voice slightly deep for a woman. 

“Yeah…” I awkwardly reply as I look to my parents for help, the two of them holding back their laughter as they watch me struggle to converse with the young woman. I motion to them with my eyes, hoping that they could help me remember who this woman was, but all they did was laugh even harder. 

“Oh? Did you forget me already… Even though we were best friends…” The young woman acts hurt as she looks away from me, before turning back to face me with a teasing and cheeky smile. It was at that moment it all clicked in my mind, her playful and overly friendly behaviour, her familiar body, my parents’ reaction to my confusion… In an instant, I understood…

“SAMUEL?!” I screamed, shocked to see that my childhood friend had not only returned after disappearing for so many years, but also that he was now no longer a ‘he’. “WHAT IN THE WORLD HAPPENED?!”

“I go by Samantha now… I decided to try hormone therapy…” Samuel, or should I say Samantha, admits as she glances to the ground with a blush on her face, before looking back up into my eyes. “After we broke up… I decided that I would try to make myself into your ideal woman. It was tough, I had to live on the streets for a couple months while working multiple odd jobs, all the money I earned solely used for the treatment.”

“It was around the time you left for college she came back home…” Samantha’s father continues as he smiles at me, his anger and rage from the last time I saw him now almost non-existent. “I spent the years my son disappeared thinking about what I did, the moment he returned home almost as if a sign from the heavens.”

“It was about then when this stubborn old fool decided to support Samantha.” Samantha’s mother cutting in as she cut to the chase, Samantha’s father blushing in embarrassment as his emotional recollection was cut short. “Using the money we saved for her college, we decided to help Samantha with her treatment funds, our family completely supportive of her dreams.”

“So…” Samantha raises her voice to catch my attention, her cheeks blushing as she looks me in the eyes with the same look she gave me many years ago. “After all this time, after all that we’ve been through, after all that has happened… I still love you… Can we start over…?”

I began to tear up as the reason for all my hard work, all my suffering and all my joy, the person I wanted right by my side once more once again appears before me. I realised around the time Amelia had confessed to me, it wasn’t because I wanted Samuel back to being my best friend anymore. Somewhere along the line, even I wasn’t sure when, I had slowly begun developing feelings for Samuel, but I quickly dismissed them because I convinced myself I couldn’t fall in love with a guy. However, now that he returned to me as a she, I could without a doubt say that what I was feeling was my true feelings…

“Yes… I’ll be glad to…”

….

“Oh? Looks like you don’t need me to suck you anymore… I mean, you’re already all worn out…” I tease as the young woman stares at me in horror, my blowjobs, according to her, the best service I offer. I could tell one single shot was not enough to satisfy my childhood friend, her lust heightened from past experiences and her own nature, but watching her face suddenly become downcast was way too pleasurable to pass up. “I mean… Unless you can do something for me…”

“I’LL DO ANYTHING!” The young woman screams, determined, as she pounces on me, her face hovering above mine as she pins me onto the bed, her eyes filled with lust. “Anything…” Her tone changes drastically from that of a beast in heat to a seductive mistress, her smile sultry as her lips crashes into mine aggressively. Assaulting my mouth with her tongue, Samantha slips her saliva-lubricated organ past my lips and into my mouth, her tongue wrapping around mine as we dance between our lips. I fight for dominance, before pulling back submissively, only to fight back again. The war of the tongue lasted for almost ten minutes, both of our members throbbing and rubbing against each other as they kiss. 

“Then… Can you suck me off…?” I whisper as the young woman crawls over me, Samantha positioning herself in such a way that both of us could pleasure each other at the same time; a 69. Gently lowering her hips towards my face, Samantha slips the tip of her member past my welcoming lips, my teeth scraping her sensitive glans and causing the young woman to thrust into my throat. I gag as the feeling of having something hard suddenly slam against the back of my throat surprising me. 

“I’m sorry!” The young woman panics as she pulls out of my mouth, a strand of saliva connecting her tip to my tongue. “I didn’t mean to…” The young woman apologises as she glances at me through the gap between our bodies, the sight of her worried face next to my half-erect shaft causing my member to fully rise to the occasion. “In apology…” Samantha trails off as she grabs onto my rod with her hands, the soft yet rough surface of her palms stimulating. 

“It’s ok…” I answer the young woman’s apology with a light peck onto her member, my kiss causing the young woman to flinch in surprise. “Let me lead this time…” I request as I place my hands onto the young woman’s back, before trailing my fingertips over her skin until they arrive at their target destination, my hands positioned such that they were holding a cheek in each of my palms. Gently pulling her butt towards me, I guide Samantha’s length into my now waiting and ready mouth, my mind prepared for something to push into my throat. 

“Mmm… It feels so warm…” Samantha moans as she lightly rocks her hips against my face, my hands holding her steady so as to prevent any unnecessary raping. “Can you… Lick the tip…” Samantha meekly requests as her member twitches in my mouth, almost as if it was seeking out something. With a smile, I gently prod at the intruder with the tip of my tongue, the taste of Samantha’s slightly dirty member coating my tongue as my saliva begins to work on her shaft, the liquid in my mouth now rich with her taste. “That feels so good… I guess it’s my turn…” 

“Ah!” I accidentally let out my voice as Samantha latches onto the sensitive tip of my shaft with her mouth, the sudden and immediate vacuum sending a mixture of pleasure and pain signals to my brain. “Sam… Slow down a bit…” I humbly request as Samantha’s reversal catches me off guard, the surprise factor alone already coaxing out a tiny bit of cream from my balls. 

“Why should I?” Samantha giggles teasingly as she moves away from my dark red tip, her saliva left coating my aroused member. “I like the way you moan like a girl sometimes… makes me feel sadistic…” Samantha confesses as she lightly blows onto my aroused tip, the cold air coming into contact with the layer of liquid that wrapped around my member creating an icy cool and stimulating sensation. 

“AH!” I gasp in shock as the pleasure hits me, my hips launching into the air on reflex. Almost as if it was an intentional act of revenge, the reflex upwards thrust of my hips coincidentally launched my tip straight into Samantha’s mouth, my engorged red tip easily slipping past her slightly agape lips and deep into her throat. Unable to brace herself for the sudden invader, Samantha lets out a short but powerful gagging noise, the vibrations from her voice causing a rippling effect on the walls of her throat. With warm walls gently massaging my length and a warm feeling against the tip of my rod, which I did not want to think about, Samantha’s impromptu deepthroat successfully lures out the cum hiding deep inside me, a powerful torrent of white fluid dumping itself into Samantha’s sea of stomach acid. “I’m sorry…”

“AT LEAST WARN ME YOU ASSHOLE!” Samantha angrily screams as she clutches her mouth with her hands, a pale look on her face. “I can still feel your sticky cream stuck to my throat… I think I’m gonna hurl…” Samantha explains between short gags as she holds herself back, a pained expression on her face. 

…..

“Are you better?” I ask, worried, after twenty minutes of hearing my lover gag and force it back, Samantha’s face aged and pale. “I didn’t mean to force myself into your throat, nor did I intend to cum straight into your body without any warning, it just kind of happened you know?” I apologise whole-heartedly as I hand Samantha a glass of warm water, her glare piercing my soul and gently stroking the dark beast of guilt inside it. 

“Sorry is not gonna make this pain go away…” Samantha bitterly fires as she rotates between glaring at me, avoiding my apologetic glance and crunching up the muscles around her eyes to deal with tha pain. “God I feel terrible…”

“I’m sorry…” I could only apologise as I stare at the ground like a kid that was caught breaking the rules, no amount of sincere apologies enough to break the tension in the air. Countless solutions raced through my head as I attempted to find a way to get back onto my lover’s good side, a way to match her suffering and at the same time express my love for her. It was then it hit me, there was only one thing I could do that could possibly fix our relationship, one thing that I had been repeatedly refusing to partake in. “To make up for it…” I hesitate before making up my mind, my body forcing myself to turn around such that my back was now facing my girlfriend. “I will let you… put it in…” I hesitate once more before finally presenting my virgin rosebud as an apology gift.

“Are you sure?” Samantha asks, now with concern in her voice instead of hostility. The both of us knew that I wasn’t comfortable with having my butt penetrated, even oral took me a while to get sued to, but that only showed how much I desperately wanted to make it up to her. “This is your anal virginity you know? It’s not something you can get back…” Samantha confirms my decision once more, the girly part of her taking things like virginities and what not seriously. I only return her question with a smile, something small like a virginity not enough to replace the bond that we had. “Ok… If you’re so sure…” 

“I’m ready… Just, please, ready me up before you put it in…” I make one final request before I completely offer myself, the fear and hesitation still running rampant inside my heart. I wasn’t ready for this, now way I was, even a finger seems like it would be too big to fit inside my ass, but now I was supposed to be able to accept something as thick and long as Samantha’s tool? The mere thought of it causes me to shudder. 

“Don’t worry… I’ll make sure to warm you right up…” Samantha snickers as the sound of her saliva lubing up her finger echoes throughout the quiet room, the sound alone making my heart beat faster. “Well then… here I go…” Samantha prepares me as she places her warm finger against my tight ring, an itchy feeling welling up from where she was poking and prodding. I groan as I feel Samantha’s nail slowly inch its way into my rectum, the warm invader only growing in size as the rest of her finger slowly crawls into my dark cave, the warmth of her body spreading through my own from our small point of connection. “God… You’re a bit too tight for me I reckon…” 

“Don’t… Worry…” I remark between groans and pants as I flash a small smile at my childhood friend. “Don’t you… remember… uhh… I’m good with… ooh… pain…” I hold back my pain-filled groans as I try my best to smile, a little bit of pain not stopping me from mending our recently mended relationship, a little pain incomparable to losing her again.

“If you say so…” Samantha sighs as she recalls how stubborn I was, her finger slowly sliding out of my insides as my iron ring tightens back to its original size. “Hold on a moment… I’m just gonna go and grab some anal lube from the kitchen.” Samantha informs as she walks away from my vulnerable form, her words slightly bewildering. 

“WHY IS THERE ANAL LUBE IN THE KITCHEN?!” I scream loud enough such that Samantha, in the other room, could hear me loud and clear, the oddity of the situation making me forget about the pain in my rear. 

“DUH!” Samantha screams back as she reappears in front of me, a large bottle of cloudy fluid in her hands. “It’s so that I can use our cucumbers to masturbate when you’re not around.” Samantha replies matter-of-factly as the most disgusting words I had heard all day easily rolls off her tongue as if she was telling me that we were having salad for dinner. 

“YOU DO WHAT WITH OUR VEGETABLES?!” I could only scream my shock as the memories of eating a cucumber only salad floods back into my mind, the image of the young woman sticking the large and elongated up her ass, pulling it out and using it for dinner making my stomach churn.

“Relax…” Samantha giggles as she dumps a load of lube into her hands, her normal smile guiltlessly on her face. “I make sure to wash them and wipe them before using it in our food… Besides, what’s a little anal juice matter to you? You’ve lick my ass countless times already.” 

“But there’s a difference in eating ass and eating sh- aH!” I cut myself off with a shriek as I feel Samantha’s finger once again slip into my anal chamber, the lubrication she had brought with her making entry much easier and smoother than before. “Don’t just stick your finger up my ass on your own will… At least warn me first…” 

“Well you were starting to rant and I was getting impatient… ah! I’m sticking another finger in now…” Samantha explains as she pushes yet another finger into my ass, her right index and middle finger making themselves comfortable inside the warm confines of my butt. 

“I just said to tell me before you do these things…” I sigh as I realise that no matter how much I lecture her, this young woman will never change. With nothing left but to accept her selfishness, I let Samantha do as she pleases with my body, her two fingers constantly wriggling about inside my body as she loosens my hole up. 

….

“Seems like you’re just about ready…” Samantha decides after preparing my body for an hour, a small pool of pre already formed and still growing under me. With another application of lube, on both her tool and my already dripping wet hole, Samantha presses her tip against my rosebud, before stopping in her tracks and leaning over me. “Are you sure about this? I’m happy that you are willing to give up such an important part of you, but I don’t want you to feel forced into this…” Samantha whispers into my ears as her breasts press against my back, both the ticklish sensations coming from my sensitive ears and the natural male instinct from having a pair of marvellous mounds against my body causing me to finally lose all composure, the desire to fuck or be fucked now burning like a raging inferno inside my body. 

“I’m ready…” I brace myself as I both tighten all the muscles in my body, while at the same time relaxing only the muscles around my anus, a feat that could only be done by master anal lovers… of which I was not.

“Loosen up Steven…” Samantha chuckles as a deep blush spreads across my face, my attempt at impressing the girl failing miserably. “You don’t have to be so tense… I’ll be gentle…” Samantha seductively whispers as she gently reaches around for my own proudly erected shaft, her fingers wrapping around my length gently before tightening into a nice and snug hold. Although Samantha’s fingers were slightly thicker than many would have liked, being born a man did have its perks. The main benefit was that handjobs were slightly more pleasurable compared to the same act when done with a natural woman, having the same tool clearly making one more masterful at the art than another. “That’s it…”

“Please be a little… ooh… gentler…” I groan as I feel my anal walls spit apart, Samantha’s girth slowly pushing inch by inch past the tight and tiny hole, the feeling of being filled bringing forth a weird mixture of pain and pleasure. It felt like my ass was on fire, an itchy burning feeling sprouting from wherever Samantha had touched, but it made her handjob that much better. Almost as if it was countering the pain, a surge of pleasure rushes through my body whenever Samantha’s fingers stroke my length, the feeling in my backdoor slowly transforming from that of pain to slight discomfort.

“Ooh~ Your butt feels so good…” Samantha moans as she slowly pulls out from my body, my intestinal walls feeling it every time she pulled at my skin with her lower head. I groaned in discomfort as I felt my internal lining being forced out of my body, the innermost part of my body still improperly lubricated. “I’m gonna go a bit faster now.” Samantha warns as she began to rock against my body, the thrusting of her hips gently increasing in both speed and force as she began to pick up the pace. “Oh god! You’re so tight…”

“Slow down…” I beg unto deaf ears as Samantha ignores my pleas, her mind probably flooded with endorphins as she continues to thrust into my butt. Thankfully, most likely because of the hour long preparation and intense amount of lubrication, the pain in my butt began to disappear as the love making continued, Samantha slowly picking up the pace as the sounds of her groin slamming against my butt echoes throughout our bedroom. “Ow…” I wince in pain as I began to feel my insides grab onto Samantha’s member, the skin around my butthole now burning in pain and screaming tobe scratched. 

“Oh… Looks like you dried up…” Samantha remarks as she, noticing both my discomfort and a sudden dryness between her thrusts, slows down. “Give me a moment… I’ll just use some temporary lube…” 

“Hm?” I turn to face my lover, my chest tightening and my shaft throbbing as soon as I did. With a cheeky smile on her face, the young woman winks seductively at me as she lets her tongue hang out of her mouth, a long trail of saliva slowly descending onto our point of connection. I jump in surprise as I feel the cold fluid coat my asshole, my rosebud quickly relaxing itself as it detaches from Samantha’s rod, allowing for our moment to continue.

“Well… Here I go…” Samantha warns as she builds up to her former speed, her hips slamming into my own faster than before. Maybe it was because our momentary pause left her with a minor case of blue balls, but it felt to me as if Samantha was rushing to achieve for something, her thrusts now more wild and desperate. “Ooh~ Your insides feel so much nicer now that it’s not completely soaked in lube…”

“I agree…” I let out a soft moan as I began to feel pleasure from being penetrated, the balance between having a small layer between our bodies and having my insides tugged by her constantly disappearing member stimulating my arousal, although I still felt like I was a long way away from achieving my orgasm.

“Steven… I don’t think… I can hold on much longer…” Samantha warns as her thrusts became even wilder, even more desperate. I knew exactly what she was implying; a part of me ecstatic that I managed to please her, but my body was already craving for more. 

“You can’t! Hold on for a while longer!” I scream in response as I tighten my anus like a vice, holding Samantha’s member in place to prevent any further stimulation. However, it seemed like my brilliant idea proved to be a fatal mistake, the sudden tightening only heightening the young woman’s pleasure as a loud scream and a warm flood into my intestines signalled her orgasm. Samantha collapses onto the ground, breathless and exhausted, her member pulling out of my body and causing the large white load inside my ass to slowly leak out and drip down my leg. 

“That felt amazing…” Samantha comments as she catches her breath, her member already shrinking as the last drops of white ooze out of her slit. I, however, still wasn’t satisfied, the burning lust inside my loins still eager for more. Pouncing onto the young woman like a hungry predator, I easily grab hold of her quickly shrinking member, my lips hastily latching itself on her tip like a leech as my tongue roams her lower head. “Ah! Stop it Steven… I’m still sensitive…” Samantha moans as she grabs the sides of my head, her words not matching her actions as she pulls me closer to her body. I let my tongue lap up the excess cream seeping out from her shaft, whilst at the same time letting my lips stroke her length. “I think… I’m getting close again…” Samantha warns, her rod probably extremely sensitive as she quickly reaches close to another orgasm. 

“NO!” I demand selfishly as I pull my lips off her throbbing erection, my hands quickly reaching for the base of her appendage as I squeeze her member tightly, preventing any of her fluids from leaking out of her body. “I need this.” I state bluntly as I position myself directly over Samantha’s tower, my own member leaking pre as I lower my hips such that her tip was now touching my rosebud, before dropping onto her quickly. 

“AHHH!” Samantha screams in pleasure as the sudden insertion triggers her orgasm, another load deposited straight into my intestines. Without letting her catch a break, I quickly began to bounce on her member, the added cream providing suitable lubrication as I easily lift myself off and drop back down onto her shaft, my weight helping to push Samantha’s engorged red tip deep into my body, a strange feeling of being filled rising from the area around my bladder. “Steven… Stop… Please… I’m gonna cum again…” 

“Not yet… I’m almost there…” I moan as I refuse Samantha’s request, the pleasure from my lower body now bringing my very close to the release I needed. However, it seemed that my double assault proved to be too much for Samantha’s already sensitive body, her third load of our session flooding my intestines as the pressure pushes against my prostate. “THAT’S IT!” I scream in pleasure as I follow closely behind my lover, my own rod throbbing and twitching as it spews out a large jet of white cream directly onto Samantha’s limp body, drops and dribbles of white decorating her stomach, breasts and face. “I needed that…” I moan as I relax, letting Samantha shrink inside me as her multiple loads ooze out of my body and soak her crotch. 

……..

“YOU JERK!” Samantha angrily punches me as she tearfully pouts, upset not only because I pretty much raped her, but also because I left her soaked with both of our juices when she inadvertently fell asleep after our intense session. “That’s it… No more anal sex for you!” 

“Does that mean I can still fuck you?” I ask, laughing as Samantha returns to playfully beating me up, her punches purposefully weak as she gives me a warning and not a beating. The two of us quickly burst into laughter as we fall back into our regular routine, our playful nature unchanging even since we were children. 

“When do you need to leave…?” Samantha asks, her voice now hushed and saddened, the air between us now tense and filled with depressing emotions. There was a reason why I was willing to give up my anal virginity today of all days, a normal apology from me usually ending with a blowjob or the occasional deepthroat. However, today was different, today was the day I was going to take another step towards my dream. 

“Tomorrow…” I reply, holding my lover closer as I let our warmth mingle, the two of us embracing tightly until the date changed. “I promise I’ll come back…” 

“Mm.” Samantha nods as she holds back her tears, clearly upset that we had to be separated once more even though we had only reunited and started dating properly barely half a year ago. “I know… Please… Go and help those like us out there…”

“I will…” I smile as I look into Samantha’s now tear-filled eyes, our lips meeting and separating repeatedly as we engage into a romantic goodbye. “It’s been my dream since you left that day many years ago… I’m going to make sure no other child will have to go through such suffering ever again…”


End file.
